Diketone

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Diacetyl, the simplest diketone
Diacetyl, the simplest diketone

A diketone is a molecule containing two ketone carbonyl groups. The simpliest aliphatic diketone is Diacetyl 2,3 butadione.This generally requires them to be 1,2-diketones (diacetyl for example), 1,3-diketones (acetylacetone), or 1,4-diketones (hexane-2,5-dione).

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Diketones undergo similar reactions to ketones or aldehydes. They readily enolize, and many 1,3-diketones are thermodynamically stable as conjugated enols or even enolates. One such is ascorbic acid, which is more stable as an enol(ate) rather than a diketone. The enol group gives off a proton, and the charge of the resulting enolate is delocalized along the ketone-enolate system. This delocalization stabilizes the enolate counterion and makes it less likely to regain the proton, which makes ascorbic acid acidic. Also, if a diketone has ketone carbonyls separated only by one carbon, the alcohol hydrogen in the corresponding enol is hydrogen-bonded to the carbonyl oxygen, giving a stable six-membered ring (-RC=CH-OH..O=CR-).

See also: Nucleophilic addition

diketone + nucleophile → tetrahedral carbonyl addition compound

  1. diketone + alcohol + acid or base ↔ hemiacetal

EU Commission has declared that diketones (for example acetylacetone, CH3COCH2COCH3) are like dialcohols and hydroxyketones in that they are in vitro and in vivo genotoxic chemical substances and therefore have been forbidden as nutrition additives since 2005.[1]

  1. ^ - EU Commission and Diketones


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